The present invention relates to sulfonylureas, agriculturally suitable compositions containing them, and their method-of-use as preemergent and/or postemergent herbicides or plant growth regulants.
U.S. Pat. No. 4,339,267 discloses, in part, herbicidal sulfonylureas of the formula ##STR1## wherein R.sub.1 is ##STR2## X is H, CH.sub.3, OCH.sub.3, Cl or CH.sub.2 OCH.sub.3 ; Y is O or CH.sub.2 ; and
R.sub.2 is H, CH.sub.3, OCH.sub.3, F, Cl, Br, NO.sub.2, CF.sub.3, COR.sub.5, S(O).sub.m R.sub.10, SO.sub.2 NR.sub.10 R.sub.11, SO.sub.2 OCH.sub.2 CF.sub.3, SO.sub.2 OCH.sub.2 CCl.sub.3 or SO.sub.2 N(OCH.sub.3)CH.sub.3. PA0 X is CH.sub.3, C.sub.2 H.sub.5, Cl, OCH.sub.3, OC.sub.2 H.sub.5, N(CH.sub.3).sub.2 or SCH.sub.3 ; PA0 Y is H, CH.sub.3 or C.sub.2 H.sub.5 ; PA0 L is Cl, Br, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.4 alkenyloxy, OH, S(O).sub.m R.sub.5, CO.sub.2 R.sub.17 or SO.sub.2 N(CH.sub.3).sub.2 ; PA0 B is O or S(O).sub.m ; and PA0 R.sub.8 is CHF.sub.2, CF.sub.3, CH.sub.2 CF.sub.3 or CF.sub.2 CHFG where G is F, Cl, Br or CF.sub.3. PA0 X is O, S, SO or SO.sub.2 ; PA0 E is CH or N; PA0 Z is O or S; etc. PA0 E is CH or N; PA0 Z is O or S; PA0 X is O, S, SO or SO.sub.2 ; etc. PA0 m is 0 or 1; PA0 A is C.sub.1 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkenylene, each unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl; PA0 Q is, among other values, OH, CN, NR.sub.6 R.sub.7, SO.sub.2 R.sub.8 or C(OR.sub.10).sub.2 R.sub.11. PA0 m is 1 or 2; PA0 R is, among other values, H, branched or unbranched C.sub.1 -C.sub.9 alkyl which is unsubstituted or substituted by halogen, OH, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkoxy or phenyl. PA0 R.sub.9 is H, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfinyl or C.sub.1 -C.sub.4 alkylsulfonyl; PA0 R.sub.10 is H, halogen or CH.sub.3 ; PA0 R.sub.11 is a radical COR.sub.24, or a C.sub.1 -C.sub.4 alkyl group that is mono- or polysubstituted by substituents selected from CN, NO.sub.2, OH, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, etc. PA0 R is H or CH.sub.3 ; PA0 A is ##STR11## X is H, CH.sub.3, C.sub.2 H.sub.5, OCH.sub.3, OC.sub.2 H.sub.5, Cl, OCF.sub.2 H, SCH.sub.3 or N(CH.sub.3).sub.2 ; PA0 Y is O or CH.sub.2 ; PA0 Y.sub.1 is H, CH.sub.3 or C.sub.2 H.sub.5 ; PA0 R.sub.1 is QR.sub.3, --C.tbd.CR.sub.4, N.sub.3, P(W.sub.1)R.sub.5 R.sub.6, --CR.sub.7 R.sub.8 R.sub.9 or C.sub.2 -C.sub.4 alkenyl substituted with 1-3 atoms of Cl, Br or F, or with C.sub.1 -C.sub.2 alkoxy, CN, OH, NO.sub.2 or S(O).sub.n R.sub.10 ; PA0 R.sub.2 is H, F, Cl, Br, CF.sub.3, CN, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 haloalkylthio, C.sub.1 -C.sub.2 alkylsulfinyl, C.sub.1 -C.sub.2 alkylsulfonyl, CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, C.sub.3 alkenyloxy or C.sub.3 alkynyloxy; PA0 Q is O, S, SO or SO.sub.2 ; PA0 R.sub.3 is C.sub.1 -C.sub.4 alkyl substituted with halogen, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 alkylsulfinyl, C.sub.1 -C.sub.2 alkylsulfonyl, C.sub.1 -C.sub.2 haloalkoxy, C.sub.1 -C.sub.2 haloalkylthio, C.sub.1 -C.sub.2 haloalkylsulfinyl, C.sub.1 -C.sub.2 haloalkylsulfonyl, OH, CN, NH.sub.2, C.sub.1 -C.sub.2 alkylamino, di(C.sub.1 -C.sub.2)alkylamino or phenyl; or R.sub.3 is C.sub.2 -C.sub.4 alkenyl optionally substituted with the substituents mentioned above; or R.sub.3 is C.sub.2 -C.sub.4 alkynyl; PA0 R.sub.4 is H or C.sub.1 -C.sub.2 alkyl optionally substituted with halogen, OH, C.sub.1 -C.sub.2 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 haloalkoxy, CN, C.sub.2 -C.sub.3 alkoxycarbonyl, cyclopropyl or phenyl; or R.sub.4 is C.sub.3 -C.sub.6 cycloalkyl or phenyl; PA0 W.sub.1 is O or S; PA0 R.sub.5 and R.sub.6 are independently C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkylthio; PA0 R.sub.7 is H, CH.sub.3 or halogen; PA0 R.sub.8 is H or CH.sub.3 ; PA0 R.sub.9 is C(O)R.sub.11 or C.sub.1 -C.sub.2 alkyl substituted with one or more groups selected from C(O)R.sub.11, CN, NO.sub.2, C.sub.1 -C.sub.2 haloalkoxy or C.sub.1 -C.sub.2 haloalkylthio; PA0 R.sub.10 is C.sub.1 -C.sub.2 alkyl; PA0 R.sub.11 is H or C.sub.1 -C.sub.2 alkyl; and PA0 n is 0, 1 or 2; PA0 (1) when A is A-3, then R.sub.3 is other than CF.sub.2 H, CF.sub.3, CH.sub.2 CF.sub.3, CF.sub.2 CHF.sub.2, CF.sub.2 CHFCl, CH.sub.2 CHFBr or CF.sub.2 CHFCF.sub.3 ; PA0 (2) when A is A-1 or A-2 and Q is S, SO or SO.sub.2, then R.sub.3 is other than unsubstituted C.sub.3 -C.sub.4 alkenyl; PA0 (3) when R.sub.3 is substituted with OH or NH.sub.2, said substituents must be separated from Q by at least two carbon atoms; and PA0 (4) when A is A-1 or A-2, then R.sub.1 is other than CH.dbd.CBr.sub.2, CH.dbd.CHOCH.sub.3, CH.dbd.CHOC.sub.2 H.sub.5, CH.dbd.CF.sub.2 or C.sub.2 -C.sub.3 alkenyl substituted with 1-3 chlorine atoms. PA0 (1) Compounds of Formula I where PA0 (2) Compounds of Preferred 1 where PA0 (3) Compounds of Preferred 2 where PA0 (4) Compounds of Preferred 3 where PA0 (5) Compounds of Preferred 4 where A is A-1; PA0 (6) Compounds of Preferred 4 where A is A-2; PA0 (7) Compounds of Preferred 4 where A is A-3. PA0 2-(difluoromethoxy)-N-[(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)amino carbonyl]-6-methylbenzenesulfonamide, m.p. 213.degree.-215.degree. C.; PA0 2-(1,2-dichloroethenyloxy)-N-[(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-y l)aminocarbonyl]benzenesulfonamide, m.p. 208.degree.-210.degree. C.; and PA0 2-difluoromethylthio-N-[(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)amin ocarbonyl]benzenesulfonamide, m.p. 184.degree.-189.degree. C. PA0 W. Braker, J. T. Sheehan, E. R. Spitmiller and W. A. Lott, J. Am. Chem. Soc., 69, 3072 (1947); PA0 P. C. Mitter and A. Bhattacharya, Quart. J. Indian Chem. Soc., 4, 152 (1927); PA0 A. Shrage and G. H. Hitchings, J. Org. Chem., 16, 1153 (1951); PA0 W. T. Caldwell, E. C. Kornfeld and C. K. Donnell, J. Am. Chem. Soc., 63, 2188 (1941); and PA0 J. D. Fissekis, A. Myles and G. B. Brown, J. Org. Chem., 29, 2670 (1964).
U.S. Pat. No. 4,487,626 discloses, in part, herbicidal sulfonylureas of the formula ##STR3## wherein R is, among other values, H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, phenyl, CH.sub.2 L, CH(CH.sub.3)L or BR.sub.8 ;
South African Patent Application No. 81/4874, published 1/17/82, discloses herbicidal sulfonylureas of the formula ##STR4## where, in part, A is a C.sub.1 -C.sub.6 alkyl radical substituted by halogen, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, etc., or a C.sub.2 -C.sub.6 alkenyl radical which is unsubstituted or substituted by the above substituents;
South African Patent Application No. 82/5042, published 7/16/81, discloses herbicidal sulfonylureas of the formula ##STR5## where, in part, A is a C.sub.3 -C.sub.6 alkynyl group;
South African Patent Application No. 83/0441, published 7/25/83, discloses herbicidal sulfonylureas of the formula ##STR6## where, in part, X is O, S, SO or SO.sub.2 ;
South African Patent Application No. 83/3779, published 11/26/83, discloses herbicidal sulfonylureas of the formula ##STR7## wherein A is --C.tbd.CR;
South African Patent Application No. 83/6449, published 3/1/84, discloses herbicidal sulfonylureas of the formula ##STR8## where, in part, R.sub.3 is C.sub.2 -C.sub.10 alkenyl which is substituted by one or more fluorine or bromine atoms or by one or more OH, CN, NO.sub.2, etc.
European Publication Nos. 102,924 and 112,803 teach herbicidal benzenesulfonylureas, which can contain azide and phosphonate esters, respectively, in the position ortho to the sulfonylurea bridge.
South African Patent Application No. 84/2722, published 10/13/84, discloses herbicidal sulfonylureas of the formula ##STR9## where, in part, A is a radical of the formula --CR.sub.6 R.sub.7 XR.sub.8, --CR.sub.9 R.sub.10 R.sub.11 or --CHR.sub.7 SCQR.sub.21 ;